18649-64-4Relevant articles and documents
Unusual C7- versus Normal 5′-O-Dimethoxytritylation of 6-Arylpyrrolocytidine Analogs
Suchy, Mojmír,Ettles, Christie,Wisner, James A.,Matarazzo, Augusto,Hudson, Robert H. E.
, p. 8415 - 8425 (2016/09/28)
Fluorescent deoxynucleosides possessing the modified bases 6-(2-benzo[b]furyl)- and 6-(2-furyl)pyrrolocytosine (BFpC and FpC) have been synthesized along with the quencher nucleosides possessing 6-{4-[(4-dimethylamino)azo]phenyl}pyrrolocytosine (DABCYLpC) and 6-(p-nitrophenyl)pyrrolocytosine (p-NO2-PhpC) nucleobase analogs. Standard treatment of BFpC, FpC, DABCYLpC, and p-NO2-PhpC with dimethoxytrityl chloride (DMT-Cl) led to the unusual substitution on the C7 of the pyrrolocytosine skeleton. The desired 5′-O-DMT-protected nucleoside analogs were synthesized from suitably protected 5′-O-DMT cytidines. Subsequent phosphitylation smoothly afforded BFpC-, FpC-, DABCYLpC-, and p-NO2-PhpC-derived monomers suitable for standard oligonucleotide synthesis.
Formation of quaternary stereogenic centers by copper-catalyzed asymmetric conjugate addition reactions of alkenylaluminums to trisubstituted enones
Mueller, Daniel,Alexakis, Alexandre
supporting information, p. 15226 - 15239 (2013/11/06)
Alkenylaluminums undergo asymmetric copper-catalyzed conjugate addition (ACA) to β-substituted enones allowing the formation of stereogenic all-carbon quaternary centers. Phosphinamine-copper complexes proved to be particularly active and selective compared with phosphoramidite ligands. After extensive optimization, high enantioselectivities (up to 96 % ee) were obtained for the addition of alkenylalanes to β-substituted enones. Two strategies for the generation of the requisite alkenylaluminums were explored allowing for the introduction of aryl- and alkyl-substituted alkenyl nucleophiles. Moreover, alkyl-substituted phosphinamine (SimplePhos) ligands were identified for the first time as highly efficient ligands for the Cu-catalyzed ACA. Chiral synthesis made easy: The copper-catalyzed conjugate addition of alkenylaluminum reagents to 3-substituted cyclic enones allows for the formation of all-carbon chiral quaternary centers (see scheme; CuTC=copper(I) thiophene-2-carboxylate). Chiral phosphinamine (SimplePhos) ligands were found to be highly efficient for this transformation.
DIYNE COMPOSITIONS
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Page/Page column 47, (2011/02/24)
A novel class of diyne compounds and diyne salts provided herein are effective and potent Olel protein inhibitors, useful for treating fungal pathogens. Compounds, fungicides and methods are provided as novel, potent and broad spectrum antifungal agents for treatment against a wide variety of fungal pathogens in humans and animals, and in the agricultural setting.
